(3R,5aR,6R,7S,8S,9aR,10aR)-3-benzyl-6,7,8,9a-tetrahydroxydecahydropyrazino[1,2-a]indole-1,4-dione

Base Information

• Chemical Name: (3R,5aR,6R,7S,8S,9aR,10aR)-3-benzyl-6,7,8,9a-tetrahydroxydecahydropyrazino[1,2-a]indole-1,4-dione
• CAS No.: 1610027-20-7
• Molecular Formula: C₁₈H₂₂N₂O₆
• Molecular Weight: 362.382

Synonyms:(3R,5aR,6R,7S,8S,9aR,10aR)-3-benzyl-6,7,8,9a-tetrahydroxydecahydropyrazino[1,2-a]indole-1,4-dione

Chemical Property of (3R,5aR,6R,7S,8S,9aR,10aR)-3-benzyl-6,7,8,9a-tetrahydroxydecahydropyrazino[1,2-a]indole-1,4-dione

Chemical Property:

Purity/Quality:

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Technology Process of (3R,5aR,6R,7S,8S,9aR,10aR)-3-benzyl-6,7,8,9a-tetrahydroxydecahydropyrazino[1,2-a]indole-1,4-dione

There total 11 articles about (3R,5aR,6R,7S,8S,9aR,10aR)-3-benzyl-6,7,8,9a-tetrahydroxydecahydropyrazino[1,2-a]indole-1,4-dione which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 44.0%

(3aS,4S,5aS,11aR,11bR,Z)-9-benzylidene-5a-(benzyloxy)-4-hydroxy-2,2-dimethyl-3a,4,5,5a,8,9-hexahydro-[1,3]dioxolo[4,5-g]pyrazino[1,2-a]indole-7,10(11aH,11bH)-dione (1610027-19-4) → (3R,5aR,6R,7S,8S,9aR,10aR)-3-benzyl-6,7,8,9a-tetrahydroxydecahydropyrazino[1,2-a]indole-1,4-dione (1610027-20-7)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In methanol; ethyl acetate; for 4h; Inert atmosphere;

DOI:10.1021/ol500990f

Reference yield:

((3aS,4S,5S,7S,7aS)-5-(benzyloxy)-2,2-dimethylhexahydro-4,7-epoxybenzo[d][1,3]dioxol-5-yl)methanol (1610027-15-0) → (3R,5aR,6R,7S,8S,9aR,10aR)-3-benzyl-6,7,8,9a-tetrahydroxydecahydropyrazino[1,2-a]indole-1,4-dione (1610027-20-7)

Guidance literature:

Multi-step reaction with 6 steps

1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.75 h / -78 °C / Inert atmosphere

2: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 3 h / 0 - 20 °C / Inert atmosphere

3: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 6 h / Inert atmosphere

4: 2,6-dimethylpyridine / dichloromethane / 6 h / Inert atmosphere

5: potassium carbonate / methanol / 2 h / Inert atmosphere

6: palladium 10% on activated carbon; hydrogen / methanol; ethyl acetate / 4 h / Inert atmosphere

With 2,6-dimethylpyridine; oxalyl dichloride; palladium 10% on activated carbon; hydrogen; potassium carbonate; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; In methanol; dichloromethane; ethyl acetate;

DOI:10.1021/ol500990f

Reference yield:

C14H18O5 → (3R,5aR,6R,7S,8S,9aR,10aR)-3-benzyl-6,7,8,9a-tetrahydroxydecahydropyrazino[1,2-a]indole-1,4-dione (1610027-20-7)

Guidance literature:

Multi-step reaction with 7 steps

1: camphor-10-sulfonic acid / acetone / 0.17 h

2: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.75 h / -78 °C / Inert atmosphere

3: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 3 h / 0 - 20 °C / Inert atmosphere

4: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 6 h / Inert atmosphere

5: 2,6-dimethylpyridine / dichloromethane / 6 h / Inert atmosphere

6: potassium carbonate / methanol / 2 h / Inert atmosphere

7: palladium 10% on activated carbon; hydrogen / methanol; ethyl acetate / 4 h / Inert atmosphere

With 2,6-dimethylpyridine; oxalyl dichloride; palladium 10% on activated carbon; camphor-10-sulfonic acid; hydrogen; potassium carbonate; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; In methanol; dichloromethane; ethyl acetate; acetone;

DOI:10.1021/ol500990f

upstream raw materials:

((3aS,4S,5S,7S,7aS)-5-(benzyloxy)-2,2-dimethylhexahydro-4,7-epoxybenzo[d][1,3]dioxol-5-yl)methanol

(Z)-1-acetyl-3-(((3aS,4S,5S,7S,7aS)-5-(benzyloxy)-2,2-dimethylhexahydro-4,7-epoxybenzo[d][1,3]dioxol-5-yl)methylene)piperazine-2,5-dione

(3Z,6Z)-3-benzylidene-6-(((3aS,4S,5S,7S,7aS)-5-(benzyloxy)-2,2-dimethylhexahydro-4,7-epoxybenzo[d][1,3]dioxol-5-yl)methylene)piperazine-2,5-dione

(3aS,4S,5aS,11aR,11bR,Z)-9-benzylidene-5a-(benzyloxy)-4-hydroxy-2,2-dimethyl-3a,4,5,5a,8,9-hexahydro-[1,3]dioxolo[4,5-g]pyrazino[1,2-a]indole-7,10(11aH,11bH)-dione

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